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Recent Advances in the Synthesis, Functionalization and Applications of Pyrazole-Type Compounds III

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: 30 June 2025 | Viewed by 9563

Special Issue Editors

Dr. Vera L. M. Silva

E-Mail Website
Guest Editor
LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal
Interests: organic synthesis; development of sustainable organic synthesis methodologies; ohmic-heating-assisted synthesis; synthesis, functionalization and structural characterization of oxygen- and nitrogen-based heterocyclic compounds; development of molecules for medicinal applications
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Artur M. S. Silva

E-Mail Website
Guest Editor
LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal
Interests: organic chemistry; green synthetic organic chemistry; synthesis of heterocyclic compounds; natural products; NMR techniques; synthesis of new compounds with biocidal and antioxidant activities
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Pyrazoles continue to attract the interest of chemists worldwide, and to generate new chemistry, due to their remarkable biological activities and occurrence in many low-molecular-weight compounds present in several marketed drugs (e.g., Celebrex® and Viagra®). Pyrazoles are also found within a variety of agrochemicals (fungicides, insecticides, and herbicides) and are versatile scaffolds for synthetic manipulations. Due to their huge importance, this third edition of the Special Issue “Recent Advances in the Synthesis, Functionalization and Applications of Pyrazole-Type Compounds” aims to highlight the most recent advances in the chemistry of pyrazole derivatives. Owing to the success of the two previous editions of this Special Issue (the last one ranked in the top ten Special Issues that collected the most papers in 2022), this third edition aims to cover a broad range of important topics of the chemistry of these nitrogen heterocyclic compounds.

We welcome the submission of original research articles and reviews that discuss new reactivity patterns, the synthesis of pyrazoles with additional fused rings, new methods for pyrazole transformation, pyrazole metal complexes, aspects of medicinal chemistry incorporating the pyrazole system, and other important features of pyrazoles’ chemistry.

Dr. Vera L. M. Silva
Prof. Dr. Artur M. S. Silva
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • pyrazoles
  • pyrazolines
  • synthesis
  • functionalization
  • transformation
  • complexes
  • applications

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Related Special Issues

Published Papers (5 papers)

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Research

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19 pages, 2066 KiB  
Article
Diorganotin(IV) Complexes of Organoselenolato Ligands with Pyrazole Moieties—Synthesis, Structure and Properties
by Melinda Tamas, Roxana A. Butuza, Monica Dan and Anca Silvestru
Molecules 2025, 30(7), 1648; https://doi.org/10.3390/molecules30071648 - 7 Apr 2025
Viewed by 372
Abstract
Diorganotin(IV) compounds of types RR′Sn(SeCH2CH2pz)2 [R = R′ = nBu (2), Ph (3); R = 2-(Me2NCH2)C6H4, R′ = Me (4), nBu ( [...] Read more.
Diorganotin(IV) compounds of types RR′Sn(SeCH2CH2pz)2 [R = R′ = nBu (2), Ph (3); R = 2-(Me2NCH2)C6H4, R′ = Me (4), nBu (5), Ph (6)], and RR′SnX(SeCH2CH2pz) [R = 2-(Me2NCH2)C6H4, R′ = nBu, X = Cl (7), R′ = Me, X = SCN (9)], as well as [2-(Me2NCH2)C6H4](Me)Sn(NCS)2 (8), and the tin(II) Sn(SeCH2CH2pz)2 (10) (pz = pyrazole), were prepared by salt metathesis reactions between the appropriate diorganotin(IV) dichloride or dipseudohalide and Na[SeCH2CH2pz], with the latter freshly prepared from (pzCH2CH2)2Se2 (1). The solution behaviour of these compounds was investigated by multinuclear NMR (1H, 13C, 77Se, 119Sn), and the NMR spectra showed the existence of the Se–Sn bonds in solution. Compounds 4 and 5 showed decomposition in a solution of chlorinated solvents with the formation of selenium bridged dimeric species of type {[2-(Me2NCH2)C6H4](R’)Se}2 [R′ = Me (4-a), nBu (5-a)], as the single-crystal X-ray diffraction studies revealed, in contrast with compound 9, for which a monomeric structure was observed with the desired composition. The solid state structures of 4-a, 5-a, 8, and 9 revealed N→Sn intramolecular coordination of the nitrogen atom in the pendant CH2NMe2 arm. The NMR spectra suggested such a coordination at room temperature only for compound 7. Full article
(This article belongs to the Special Issue Recent Advances in the Synthesis, Functionalization and Applications of Pyrazole-Type Compounds III)
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26 pages, 4252 KiB  
Article
Synthesis and Characterization of New Pyrano[2,3-c]pyrazole Derivatives as 3-Hydroxyflavone Analogues
by Arminas Urbonavičius, Sonata Krikštolaitytė, Aurimas Bieliauskas, Vytas Martynaitis, Joana Solovjova, Asta Žukauskaitė, Eglė Arbačiauskienė and Algirdas Šačkus
Molecules 2023, 28(18), 6599; https://doi.org/10.3390/molecules28186599 - 13 Sep 2023
Cited by 3 | Viewed by 2409
Abstract
In this paper, an efficient synthetic route from pyrazole-chalcones to novel 6-aryl-5-hydroxy-2-phenylpyrano[2,3-c]pyrazol-4(2H)-ones as 3-hydroxyflavone analogues is described. The methylation of 5-hydroxy-2,6-phenylpyrano[2,3-c]pyrazol-4(2H)-one with methyl iodide in the presence of a base yielded a compound containing a [...] Read more.
In this paper, an efficient synthetic route from pyrazole-chalcones to novel 6-aryl-5-hydroxy-2-phenylpyrano[2,3-c]pyrazol-4(2H)-ones as 3-hydroxyflavone analogues is described. The methylation of 5-hydroxy-2,6-phenylpyrano[2,3-c]pyrazol-4(2H)-one with methyl iodide in the presence of a base yielded a compound containing a 5-methoxy group, while the analogous reaction of 5-hydroxy-2-phenyl-6-(pyridin-4-yl)pyrano[2,3-c]pyrazol-4(2H)-one led to the zwitterionic 6-(N-methylpyridinium)pyrano[2,3-c]pyrazol derivative. The treatment of 5-hydroxy-2,6-phenylpyrano[2,3-c]pyrazol-4(2H)-one with triflic anhydride afforded a 5-trifloylsubstituted compound, which was further used in carbon–carbon bond forming Pd-catalyzed coupling reactions to yield 5-(hetero)aryl- and 5-carbo-functionalized pyrano[2,3-c]pyrazoles. The excited-state intramolecular proton transfer (ESIPT) reaction of 5-hydroxypyrano[2,3-c]pyrazoles from the 5-hydroxy moiety to the carbonyl group in polar protic, polar aprotic, and nonpolar solvents was observed, resulting in well-resolved two-band fluorescence. The structures of the novel heterocyclic compounds were confirmed by 1H-, 13C-, 15N-, and 19F-NMR spectroscopy, HRMS, and single-crystal X-ray diffraction data. Full article
(This article belongs to the Special Issue Recent Advances in the Synthesis, Functionalization and Applications of Pyrazole-Type Compounds III)
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Review

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23 pages, 15163 KiB  
Review
The Role of Flow Chemistry on the Synthesis of Pyrazoles, Pyrazolines and Pyrazole-Fused Scaffolds
by Catarina M. Correia, Artur M. S. Silva and Vera L. M. Silva
Molecules 2025, 30(7), 1582; https://doi.org/10.3390/molecules30071582 - 2 Apr 2025
Viewed by 458
Abstract
Nitrogen-containing heterocycles are fundamental scaffolds in organic chemistry, particularly due to their prevalence in pharmaceuticals, agrochemicals and materials science. Among them, five-membered rings, containing two nitrogen atoms in adjacent positions—such as pyrazoles, pyrazolines and indazoles—are especially significant due to their versatile biological activities [...] Read more.
Nitrogen-containing heterocycles are fundamental scaffolds in organic chemistry, particularly due to their prevalence in pharmaceuticals, agrochemicals and materials science. Among them, five-membered rings, containing two nitrogen atoms in adjacent positions—such as pyrazoles, pyrazolines and indazoles—are especially significant due to their versatile biological activities and structural properties, which led to the search for greener, faster and more efficient methods for their synthesis. Conventional batch synthesis methods, while effective, often face challenges related to reaction efficiency, scalability and safety. Flow chemistry has emerged as a powerful alternative, offering enhanced control over reaction parameters, improved safety profiles and opportunities for scaling up synthesis processes efficiently. This review explores the impact of flow chemistry on the synthesis of these pivotal heterocycles, highlighting its advantages over the conventional batch methods. Although indazoles have a five-membered ring fused with a benzene ring, they will also be considered in this review due to their biological relevance. Full article
(This article belongs to the Special Issue Recent Advances in the Synthesis, Functionalization and Applications of Pyrazole-Type Compounds III)
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31 pages, 7101 KiB  
Review
Bioactive Fused Pyrazoles Inspired by the Adaptability of 5-Aminopyrazole Derivatives: Recent Review
by Dana M. Odeh, Mohanad M. Odeh, Taghrid S. Hafez and Ashraf S. Hassan
Molecules 2025, 30(2), 366; https://doi.org/10.3390/molecules30020366 - 17 Jan 2025
Cited by 1 | Viewed by 1263
Abstract
Heterocyclic compounds, especially those containing the pyrazole moiety, are highly significant in organic chemistry and possess remarkable and diverse biological properties. The 5-aminopyrazole derivatives are key starting materials for the synthesis of numerous bioactive compounds such as pyrazolopyridine, pyrazolopyrimidine, pyrazoloquinazoline, and pyrazolotriazine derivatives. [...] Read more.
Heterocyclic compounds, especially those containing the pyrazole moiety, are highly significant in organic chemistry and possess remarkable and diverse biological properties. The 5-aminopyrazole derivatives are key starting materials for the synthesis of numerous bioactive compounds such as pyrazolopyridine, pyrazolopyrimidine, pyrazoloquinazoline, and pyrazolotriazine derivatives. Many compounds inspired by the 5-aminopyrazole derivatives possess a wide spectrum of biological activities and medicinal applications such as antioxidants, anticancer agents, enzyme inhibitors, antimicrobials, and anti-tuberculosis activities. This review summarizes the recently reported synthesis methods and biological activities of fused pyrazole and pyrazole-based derivatives based on 5-aminopyrazole compounds within the last 5 years (2020 to present). One of the important goals of this review is to illustrate future strategies for the design, development, and utilization of pyrazole products as potent drugs. Full article
(This article belongs to the Special Issue Recent Advances in the Synthesis, Functionalization and Applications of Pyrazole-Type Compounds III)
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39 pages, 23502 KiB  
Review
Fluconazole Analogs and Derivatives: An Overview of Synthesis, Chemical Transformations, and Biological Activity
by Michał Janowski, Oleg M. Demchuk and Monika Wujec
Molecules 2024, 29(12), 2855; https://doi.org/10.3390/molecules29122855 - 15 Jun 2024
Cited by 6 | Viewed by 3707
Abstract
Fluconazole (2-(2,4-difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol), which was patented in 1981 and introduced for commercial use in 1988, is a widely utilized antifungal drug whose mechanism of action involves inhibition of the activity of 14-α lanosterol demethylase. Its safety and effectiveness have established it as [...] Read more.
Fluconazole (2-(2,4-difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol), which was patented in 1981 and introduced for commercial use in 1988, is a widely utilized antifungal drug whose mechanism of action involves inhibition of the activity of 14-α lanosterol demethylase. Its safety and effectiveness have established it as one of the most frequently employed antifungal agents. Resistance to azole antifungal drugs is becoming more common. It may be related to a mutation of the gene encoding the enzyme. To address this issue, molecules with modifications in three main regions of fluconazole, namely the hydroxyl group, the aromatic ring, and the 1,2,4-triazole rings, have been synthesized in an attempt to create more potent antifungal drugs. These modifications aim at enhancing the effectiveness against microorganisms and improving pharmacokinetic parameters and safety profiles of the synthesized compounds. The present review explores the synthesis of fluconazole derivatives, accompanied by insights into the results of biological studies evaluating the therapeutic effects of these compounds. Full article
(This article belongs to the Special Issue Recent Advances in the Synthesis, Functionalization and Applications of Pyrazole-Type Compounds III)
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